Whiteness has certain fixed meanings in Jamaica. Being white in a country where 95% of the population is black, but where whites still represent the upper echelons of society, produces a peculiar dilemma of privilege counterpoised by marginalization. Compounded by awareness of the past role of whites in a slave society, the dilemma of white Jamaicans is undeniable. Also undeniable, however, is the fact that the costs of being white are outweighed by the benefits, as the white Jamaican writer Anthony C. Winkler acknowledges in two autobiographical works. Winkler experiences those benefits both in black Jamaica and in white America, where he comes to fully appreciate just how much of a Jamaican he is, as well as to grasp the idiosyncrasies of Jamaican vs American constructions of whiteness vs blackness.

This paper examines issues of racial and cultural identity raised, directly or indirectly, by Winkler as a white writer of the Jamaican diaspora.

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